Intramolecular nitrile oxide-alkene cycloaddition of sugar derivatives with unmasked hydroxyl group(s)

Tony K.M. Shing, Wai F. Wong, Hau M. Cheng, Wun S. Kwok, King H. So

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

(Chemical Equation Presented) Intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar derivatives with one to four free hydroxyl group(s) is reported. The INOC reaction, using chloramine-T, in the presence of silica gel, to generate nitrile oxides from oximes, proceeded smoothly to afford five- or six-membered carbocycles in good to excellent yields. This new methodology alleviates protection/deprotection steps and makes the synthetic route shorter and more efficient.

Original languageEnglish
Pages (from-to)753-756
Number of pages4
JournalOrganic Letters
Volume9
Issue number5
DOIs
Publication statusPublished - 2007 Mar 1

    Fingerprint

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this